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- Citraconic anhydride
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2026-09-11
- CAS:616-02-4
- Min. Order: 25KG
- Purity: 98%min
- Supply Ability: 30tons/month
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| | Citraconic anhydride Basic information |
| | Citraconic anhydride Chemical Properties |
| Melting point | 6-10 °C (lit.) | | Boiling point | 213-214 °C (lit.) | | density | 1.247 g/mL at 25 °C (lit.) | | vapor density | 4 (vs air) | | vapor pressure | 1.3 hPa ( 47 °C) | | refractive index | n20/D 1.471(lit.) | | Fp | 215 °F | | storage temp. | Inert atmosphere,2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Liquid | | color | Clear colorless to very slightly yellow | | Water Solubility | decomposes | | Sensitive | Moisture Sensitive | | BRN | 1835 | | Dielectric constant | 40.3(20℃) | | InChI | 1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3 | | InChIKey | AYKYXWQEBUNJCN-UHFFFAOYSA-N | | SMILES | CC1=CC(=O)OC1=O | | LogP | -0.232 (est) | | CAS DataBase Reference | 616-02-4(CAS DataBase Reference) | | NIST Chemistry Reference | 2,5-Furandione, 3-methyl-(616-02-4) | | EPA Substance Registry System | 2,5-Furandione, 3-methyl- (616-02-4) |
| | Citraconic anhydride Usage And Synthesis |
| Chemical Properties | clear colorless to very slightly yellow liquid | | Uses | Versatile reagent used for the synthesis of maleimides, bicyclic pyrrolidines, and co- and terpolymers, as well as for the protection of N-terminal amino acids. | | Uses | Citraconic anhydride is used as a monomer for specialty unsaturated polyester resins. It is used to prepare bicyclic pyrrolidines, maleimides and co- and terpolymers. It is also used for the protection of N-terminal amino acids. Further, it is involved in the preparation of clothing ping acid and its amide. In addition to this, it is selectively used for the isolation of histidyl peptides. | | Uses | Reagent for alkalies, alcohols, and amines. | | Application | Citraconic anhydride(methylmaleic anhydride) is a versatile compound. It may be used in the synthesis of antireversion agents used in the rubber industry or in the copolymerisation, e.g. with styrene. On a smaller scale, it is studied as a building block for the synthesis of strigol-type germination stimulants or of chemotherapy drugs[2]. | | General Description | Citraconic anhydride is a reversible blocking agent for the lysine side chain. A major advantage of the citraconic anhydride reaction is that the blocking group can be readily removed without causing protein denaturation[1]. | | Flammability and Explosibility | Non flammable | | Reactions |
Citraconic anhydride is highly reactive due to the presence of anhydride groups and can undergo hydrolysis, esterification, amidation, and addition reactions.
| | Chemical Reactivity |
Citraconic anhydride (CA) is defined as a derivative of maleic anhydride that reacts with amines to form amide linkages at alkaline pH and can be hydrolyzed at acidic pH to release citraconic acid and free the amine, making it useful for temporarily blocking amine groups during molecular modifications.
| | Synthesis |
Citraconic anhydride was prepared by using alkaline earth metal oxides or alkaline earth metal sulfates as catalysts, and reacting for 1.0-10.0h at a mass ratio of itaconic acid and catalyst of 50:1 to 500:1, a mass ratio of itaconic acid and solvent of 1:1 to 1:10, and a reaction temperature of 130-210C, and recovering and reusing solvents;
Said alkaline earth metal oxide or alkaline earth metal sulfate catalyst is one of magnesium oxide, calcium oxide, barium oxide, strontium oxide, magnesium sulfate, calcium sulfate, barium sulfate, and strontium sulfate; and said solvent is one of xylene, o-dichlorobenzene, and tetrahydronaphthalene.
| | Purification Methods | Possible contamination is from the acid formed by hydrolysis. If the IR has OH bands, then reflux with Ac2O for 30minutes, evaporate, then distil the residue in a vacuum, otherwise distil in a vacuum. Store in a dry atmosphere. [Vaughan & Andersen J Am Chem Soc 77 6702 1955, Vaughan & Andersen J Org Chem 21 680 1956, Beilstein 17 H 440, 17 I 234, 17 II 448, 17 III/IV 5912, 17/11 V 65.] | | References | [1] Simpson, R. J. (2006). Modification of lysyl side chains using citraconic anhydride. CSH Protocols, 2006 5. https://doi.org/10.1101/pdb.prot4552
[2] R Philipps, M. A. L., St Walter. (2002). Selective oxidation of isoprene to citraconic anhydride. Chemical Engineering Journal, 90 1, Pages 107-116. https://doi.org/10.1016/S1385-8947(02)00072-4
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| | Citraconic anhydride Preparation Products And Raw materials |
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